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MetaCyc Compound: iodoacetate

Synonyms: 2-iodoacetate, monoiodoacetate

Superclasses: an organohalogen compoundan organoiodine compound

Chemical Formula: C2H2O2I

Molecular Weight: 184.94 Daltons

Monoisotopic Molecular Weight: 185.9177723405 Daltons

iodoacetate compound structure


InChI: InChI=1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)/p-1


Unification Links: ChemSpider:452795, PubChem:519093

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -61.249817Inferred by computational analysis [Latendresse13]

Enzymes inhibited by iodoacetate, sorted by the type of inhibition, are:

Inhibitor (Noncompetitive) of: aspartate semialdehyde dehydrogenase [Hegeman70, Helmward89] Inhibitor (Mechanism unknown) of: lactaldehyde dehydrogenase [Sridhara69], glyceraldehyde 3-phosphate dehydrogenase [DAlessio71a], ribose-5-phosphate isomerase [Essenberg75a], NADPH-dependent curcumin reductase [Hassaninasab11], S-formylglutathione hydrolase [Gonzalez06a], S-formylglutathione hydrolase [Gonzalez06a], limit dextrin α-1,6-glucohydrolase [Jeanningros76], 2-keto-4-hydroxyglutarate aldolase, 2,3,4-saturated fatty acyl-[acp]:NAD+ oxidoreductase [Weeks68], biotin sulfoxide reductase [Del79], riboflavin reductase [Fontecave87], lactose 2-epimerase [Taguchi08], 3-hydroxybenzyl alcohol dehydrogenase [Forrester72], cellobiose 2-epimerase [Taguchi08], synephrine dehydratase [Manne86], o-dihydric phenol O-methyltransferase (para-methylation) [Tsang79], esculetin 6-O-methyltransferase (meta-methylation) [Tsang79], 4-oxalocrotonate decarboxylase [Orii06], 4-oxalocrotonate tautomerase [Orii06], 2-hydroxymuconate 6-semialdehyde dehydrogenase [Orii06], 2-amino-5-carboxymuconic 6-semialdehyde deaminase [Orii04], sequoyitol dehydrogenase [Ruis69], NAD+-dependent L-rhamnofuranose 1-dehydrogenase [Rigo76], N-cyclohexylformamide hydratase [Goda01], glycocholate hydrolase [Tanaka00], 5-dehydro-4-deoxy-D-glucarate dehydratase [Dagley75], L-dopa O-methyltransferase [Axelrod58], [thyroglobulin]-3,5-diiodotyrosine synthase [Coval67], carnitine O-acetyltransferase [Miyazawa83], deacetoxycephalosporin C hydroxylase [Baker91], ethylnitronate monooxygenase [Gorlatova98], proline racemase [Cardinale68], 2,4-diaminopentanoate dehydrogenase [Somack73a], 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase [Maruyama78], factor-independent urate hydroxylase [Bachrach57], choline dehydrogenase [Nagasawa76], (indol-3-yl)acetaldehyde:oxygen oxidoreductase [Koiwai00], p-hydroxybenzoate hydroxylase [Hosokawa66], isethionate dehydrogenase [Kondo77], guanidinoacetate methyltransferase [Fujioka88], tryptophan decarboxylase [Buki85], D-ornithine aminomutase, ornithine cyclodeaminase [Muth74], Δ1-pyrroline-3-hydroxy-5-carboxylate dehydrogenase [Adams60], hydroxyproline 2-epimerase [Adams64], D-galactonate dehydratase [Szumilo81], L-sorbosone dehydrogenase [Asakura99], L-sorbosone dehydrogenase [Miyazaki06], triosephosphate isomerase [Kurzok84], triosephosphate isomerase [Kurzok84], maleylacetoacetate isomerase [Seltzer73], ethylnitronate monooxygenase [Kido76] Inhibitor (Other types) of: biotin transporter [Prakash74], D-proline dehydrogenase [Tanigawa10], D-amino acid dehydrogenase [Tanigawa10], L-sorbose dehydrogenase [Sugisawa91], sulfite dehydrogenase [Nakamura95], sulfur oxygenase reductase [Kletzin89], methylglyoxal reductase (NADH-dependent) [Ting65], thiosulfate reductase [Aketagawa85]

This compound has been characterized as an alternative substrate of the following enzymes: bromoacetate dehalogenase


Adams60: Adams, E., Goldstone, A. (1960). "Hydroxyproline metabolism. IV. Enzymatic synthesis of gamma-hydroxyglutamate from Delta 1-pyrroline-3-hydroxy-5-carboxylate." J Biol Chem 235;3504-12. PMID: 13681370

Adams64: Adams E, Norton IL (1964). "Purification and properties of inducible hydroxyproline 2-epimerase from Pseudomonas." J Biol Chem 239;1525-35. PMID: 14189888

Aketagawa85: Aketagawa J, Kobayashi K, Ishimoto M (1985). "Purification and properties of thiosulfate reductase from Desulfovibrio vulgaris, Miyazaki F." J Biochem (Tokyo) 97(4);1025-32. PMID: 2993256

Asakura99: Asakura A, Hoshino T (1999). "Isolation and Characterization of a New Quinoprotein Dehydrogenase, L-Sorbose/L-Sorbosone Dehydrogenase." Biosci. Biotechnol. Biochem., 63 (1), 46-53.

Axelrod58: Axelrod J, Tomchick R (1958). "Enzymatic O-methylation of epinephrine and other catechols." J Biol Chem 233(3);702-5. PMID: 13575440

Bachrach57: Bachrach, U (1957). "The aerobic breakdown of uric acid by certain pseudomonads." J Gen Microbiol 17(1);1-11. PMID: 13475666

Baker91: Baker BJ, Dotzlaf JE, Yeh WK (1991). "Deacetoxycephalosporin C hydroxylase of Streptomyces clavuligerus. Purification, characterization, bifunctionality, and evolutionary implication." J Biol Chem 266(8);5087-93. PMID: 2002049

Buki85: Buki KG, Vinh DQ, Horvath I (1985). "Partial purification and some properties of tryptophan decarboxylase from a Bacillus strain." Acta Microbiol Hung 32(1);65-73. PMID: 4036551

Cardinale68: Cardinale GJ, Abeles RH (1968). "Purification and mechanism of action of proline racemase." Biochemistry 1968;7(11);3970-8. PMID: 5722267

Coval67: Coval ML, Taurog A (1967). "Purification and iodinating activity of hog thyroid peroxidase." J Biol Chem 242(23);5510-23. PMID: 12325367

Dagley75: Dagley S, Jeffcoat R (1975). "D-4-deoxy-5-ketoglucarate hydro-lyase (decarboxylating)." Methods Enzymol 42;272-6. PMID: 237186

DAlessio71a: D'Alessio G, Josse J (1971). "Glyceraldehyde phosphate dehydrogenase of Escherichia coli. Structural and catalytic properties." J Biol Chem 246(13);4326-33. PMID: 4326214

Del79: Del Campillo-Campbell, A, Dykhuizen, D, Cleary, PP "Enzymatic reduction of d-biotin d-sulfoxide to d-biotin." Methods in Enzymology 62:379-385 (1979).

Essenberg75a: Essenberg MK, Cooper RA (1975). "Two ribose-5-phosphate isomerases from Escherichia coli K12: partial characterisation of the enzymes and consideration of their possible physiological roles." Eur J Biochem 55(2);323-32. PMID: 1104357

Fontecave87: Fontecave M, Eliasson R, Reichard P (1987). "NAD(P)H:flavin oxidoreductase of Escherichia coli. A ferric iron reductase participating in the generation of the free radical of ribonucleotide reductase." J Biol Chem 1987;262(25);12325-31. PMID: 3305505

Forrester72: Forrester PI, Gaucher GM (1972). "m-Hydroxybenzyl alcohol dehydrogenase from Penicillium urticae." Biochemistry 11(6);1108-14. PMID: 4335290

Fujioka88: Fujioka M, Konishi K, Takata Y (1988). "Recombinant rat liver guanidinoacetate methyltransferase: reactivity and function of sulfhydryl groups." Biochemistry 27(20);7658-64. PMID: 3207695

Goda01: Goda M, Hashimoto Y, Shimizu S, Kobayashi M (2001). "Discovery of a novel enzyme, isonitrile hydratase, involved in nitrogen-carbon triple bond cleavage." J Biol Chem 276(26);23480-5. PMID: 11306561

Gonzalez06a: Gonzalez CF, Proudfoot M, Brown G, Korniyenko Y, Mori H, Savchenko AV, Yakunin AF (2006). "Molecular basis of formaldehyde detoxification: Characterization of two s-formylglutathione hydrolases from Escherichia coli, FrmB and YeiG." J Biol Chem 281:14514-14522. PMID: 16567800

Gorlatova98: Gorlatova N, Tchorzewski M, Kurihara T, Soda K, Esaki N (1998). "Purification, characterization, and mechanism of a flavin mononucleotide-dependent 2-nitropropane dioxygenase from Neurospora crassa." Appl Environ Microbiol 1998;64(3);1029-33. PMID: 9501443

Hassaninasab11: Hassaninasab A, Hashimoto Y, Tomita-Yokotani K, Kobayashi M (2011). "Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism." Proc Natl Acad Sci U S A 108(16);6615-20. PMID: 21467222

Hegeman70: Hegeman G, Cohen G, Morgan R "Aspartic semialdehyde dehydrogenase (Escherichia coli K12)." Methods in Enzymology 1970; 17A:708-713.

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

Hosokawa66: Hosokawa K, Stanier RY (1966). "Crystallization and properties of p-hydroxybenzoate hydroxylase from Pseudomonas putida." J Biol Chem 241(10);2453-60. PMID: 4380381

Jeanningros76: Jeanningros R, Creuzet-Sigal N, Frixon C, Cattaneo J (1976). "Purification and properties of a debranching enzyme from Escherichia coli." Biochim Biophys Acta 1976;438(1);186-99. PMID: 779849

Kido76: Kido T, Soda K, Suzuki T, Asada K (1976). "A new oxygenase, 2-nitropropane dioxygenase of Hansenula mrakii. Enzymologic and spectrophotometric properties." J Biol Chem 251(22);6994-7000. PMID: 11214

Kletzin89: Kletzin A (1989). "Coupled enzymatic production of sulfite, thiosulfate, and hydrogen sulfide from sulfur: purification and properties of a sulfur oxygenase reductase from the facultatively anaerobic archaebacterium Desulfurolobus ambivalens." J Bacteriol 171(3);1638-43. PMID: 2493451

Koiwai00: Koiwai H, Akaba S, Seo M, Komano T, Koshiba T (2000). "Functional expression of two Arabidopsis aldehyde oxidases in the yeast Pichia pastoris." J Biochem (Tokyo) 2000;127(4);659-64. PMID: 10739959

Kondo77: Kondo H, Niki H, Takahashi S, Ishimoto M (1977). "Enzymatic oxidation of isethionate to sulfoacetaldehyde in bacterial extract." J Biochem (Tokyo) 81(6);1911-6. PMID: 197072

Kurzok84: Kurzok H.-G., Feierabend J. (1984). "Comparison of a cytosolic and a chloroplast trioseohosphate isomerase isoenzyme from rye leaves." Bioch. Biophys. Acta 788:214-221.

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Manne86: Manne V, Kutty KR, Pillarisetti SR (1986). "Purification and properties of synephrinase from Arthrobacter synephrinum." Arch Biochem Biophys 248(1);324-34. PMID: 3729420

Maruyama78: Maruyama K, Ariga N, Tsuda M, Deguchi K (1978). "Purification and properties of alpha-hydroxy-gamma-carboxymuconic epsilon-semialdehyde dehydrogenase." J Biochem (Tokyo) 83(4);1125-34. PMID: 26671

Miyazaki06: Miyazaki T, Sugisawa T, Hoshino T (2006). "Pyrroloquinoline quinone-dependent dehydrogenases from Ketogulonicigenium vulgare catalyze the direct conversion of L-sorbosone to L-ascorbic acid." Appl Environ Microbiol 72(2);1487-95. PMID: 16461703

Miyazawa83: Miyazawa S, Ozasa H, Furuta S, Osumi T, Hashimoto T (1983). "Purification and properties of carnitine acetyltransferase from rat liver." J Biochem 93(2);439-51. PMID: 6404901

Muth74: Muth WL, Costilow RN (1974). "Ornithine cyclase (deaminating). II. Properties of the homogeneous enzyme." J Biol Chem 249(23);7457-62. PMID: 4373469

Nagasawa76: Nagasawa, T., Mori, N., Tani, Y., Ogata, K. (1976). "Characterization of choline dehydrogenase from Pseudomonas aeruginosa A-16." Agr. Biol. Chem. 40(10):2077-2084.

Nakamura95: Nakamura, K., Yoshikawa, H., Okubo, S., Kurosawa, H., Amano, Y. (1995). "Purification and properties of membrane-bound sulfite dehydrogenase from Thiobacillus thiooxidans." JCM 7814. Biosci. Biotechnol. Biochem. 59: 11-15.

Orii04: Orii C, Takenaka S, Murakami S, Aoki K (2004). "A novel coupled enzyme assay reveals an enzyme responsible for the deamination of a chemically unstable intermediate in the metabolic pathway of 4-amino-3-hydroxybenzoic acid in Bordetella sp. strain 10d." Eur J Biochem 271(15);3248-54. PMID: 15265044

Orii06: Orii C, Takenaka S, Murakami S, Aoki K (2006). "Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: A different modified meta-cleavage pathway for 2-aminophenols." Biosci Biotechnol Biochem 70(11);2653-61. PMID: 17090920

Prakash74: Prakash O, Eisenberg MA (1974). "Active transport of biotin in Escherichia coli K-12." J Bacteriol 120(2);785-91. PMID: 4616949

Rigo76: Rigo LU, Nakano M, Veiga LA, Feingold DS (1976). "L-rhamnose dehydrogenase of Pullularia pullulans." Biochimica et Biophysica Acta 445, 286-293.

Ruis69: Ruis H, Hoffmann-Ostenhof O (1969). "Enzymic epimerization of sequoyitol to D-pinitol in Trifolium incarnatum." Eur J Biochem 7(3);442-8. PMID: 4389340

Seltzer73: Seltzer S (1973). "Purification and properties of maleylacetone cis-trans isomerase from vibrio 01." J Biol Chem 248(1);215-22. PMID: 4692831

Somack73a: Somack R, Costilow RN (1973). "2,4-diaminopentanoic acid C 4 dehydrogenase. Purification and properties of the protein." J Biol Chem 1973;248(2);385-8. PMID: 4684685

Sridhara69: Sridhara S, Wu TT (1969). "Purification and properties of lactaldehyde dehydrogenase from Escherichia coli." J Biol Chem 1969;244(19);5233-8. PMID: 4310089

Sugisawa91: Sugisawa, T., Hoshino, T., Nomura, S., Fujiwara, A. (1991). "Isolation and characterization of membrane-bound L-sorbose dehydrogenase from Gluconobacter melanogenus UV10." Agric. Biol. Chem. 55(2): 363-370.

Szumilo81: Szumilo T (1981). "Purification and properties of D-galactonate dehydratase from Mycobacterium butyricum." Biochim Biophys Acta 661(2);240-6. PMID: 7295736

Taguchi08: Taguchi H, Hamada S, Kawauchi S, Ito H, Senoura T, Watanabe J, Nishimukai M, Ito S, Matsui H (2008). "Enzymatic properties of cellobiose 2-epimerase from Ruminococcus albus and the synthesis of rare oligosaccharides by the enzyme." Appl Microbiol Biotechnol 79(3);433-41. PMID: 18392616

Tanaka00: Tanaka H, Hashiba H, Kok J, Mierau I (2000). "Bile salt hydrolase of Bifidobacterium longum-biochemical and genetic characterization." Appl Environ Microbiol 66(6);2502-12. PMID: 10831430

Tanigawa10: Tanigawa M, Shinohara T, Saito M, Nishimura K, Hasegawa Y, Wakabayashi S, Ishizuka M, Nagata Y (2010). "D-Amino acid dehydrogenase from Helicobacter pylori NCTC 11637." Amino Acids 38(1);247-55. PMID: 19212808

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Weeks68: Weeks G, Wakil SJ (1968). "Studies on the mechanism of fatty acid synthesis. 18. Preparation and general properties of the enoyl acyl carrier protein reductases from Escherichia coli." J Biol Chem 1968;243(6);1180-9. PMID: 4384650

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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